Hydrochloric Acid → HCID 15287673, compound

HRID 1655425Notes

Reaction equation

HRID 1655425 reaction equation
[CH3:1][C:2]([C:5]1[CH:10]=[C:9]([SH:11])[CH:8]=[C:7]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:6]=1[OH:16])([CH3:4])[CH3:3].[O-]CC.[Na+].[CH:21]12[O:27][CH:22]1[CH2:23][CH2:24][CH2:25][CH2:26]2.Cl>C(O)C>[CH3:13][C:12]([C:7]1[CH:8]=[C:9]([S:11][C@@H:21]2[CH2:26][CH2:25][CH2:24][CH2:23][C@H:22]2[OH:27])[CH:10]=[C:5]([C:2]([CH3:1])([CH3:3])[CH3:4])[C:6]=1[OH:16])([CH3:15])[CH3:14]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 9246Cyclohexene oxideHCID 703702,6-Di-tert-butyl-4-mercaptophenolHCID 2723922Sodium ethoxide

Product 1

HCID 15287673HCID 15287673, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2,6-bis(1,1-Dimethylethyl)-4-mercaptophenol (12.8 g, 0.054 moles) was added to a solution of sodium ethoxide [prepared from sodium (2.5 g 0.108 mole)] in ethyl alcohol (75 ml). Cyclohexene oxide (5.15 g, 0.0525 mole) was added and the reaction mixture was stirred at room temperature for 20 hours. The reaction mixture was poured into 10% hydrochloric acid (250 ml) and the mixture was extracted twice with 200ml of ethyl ether. The combined ethyl ether extracts were washed twice with 25 ml of water, dried over magnesium sulfate, filtered and concentrated in vacuo to a yellow oil. The product was purified by silica get chromatography and recrystallized from methyl alcohol/water, m.p. ca 91° C. The structure was supported by NMR, infrared spectroscopy, and elemental analysis.

Workup

  1. extractionthe mixture was extracted twice with 200ml of ethyl ether
  2. washThe combined ethyl ether extracts were washed twice with 25 ml of water
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo to a yellow oil
  6. customThe product was purified by silica
  7. customget chromatography
  8. customrecrystallized from methyl alcohol/water, m.p. ca 91° C

Sources & evidence

ORD record
ord-dd5136425bb64fb2a6738a42dd72f9c9
Source dataset
uspto-grants-1993_10
Patent number
US05250567

Reaction notes

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